"World of Dance" judge Derek Hough joins Bear on a whirlwind adventure across the mountains of Bulgaria. Dropped amidst snow-capped peaks, Derek and Bear must ascend a jagged mountain ridge, make a steep rappel with Derek's cell phone as their only safety, and swim a freezing lake to reach their destination. But a surprise, death-defying final challenge will test Derek like nothing before. Along the way, Derek reveals his struggles with being bullied as a child, his devotion to his craft, and teaches Bear some much-needed dance moves.

Tennis great Roger Federer joins Bear on a grand slam journey through the Swiss Alps. After meeting up amidst stunning snow-capped peaks, Bear and Roger descend a frozen waterfall and use tennis rackets as snowshoes to cross a frozen lake. After a quick snack of fish eyeballs, the pair get creative with a tennis ball to ascend a steep cliff that is their only way home. Along the way, Roger discusses the hard work it takes to achieve victory, his amusing experiences raising two sets of twins, and takes on the challenge when Bear invites him to a hilarious match of ping pong.